In yesterday’s post, I said:

Managers have a significant impact on your career and work experience. They can eliminate obstacles in your path, offer timely guidance on things you’re not seeing, and put in a good word for you with the right people.

I did things the hard way that summer. Don’t be like me.

Bring your people along.

My friend Sana asked in response:

“Would your advice change if your manager wasn’t generally helpful or lacked the skills to be?”

Yes.

The bedrock of any healthy management relationship is trust, and not everyone is afforded this luxury. Managers are people, and people are sometimes toxic. This toxicity can permeate the culture of a team and organization in a way that leads to a lack of psychological safety for its people.

Mentors, advisors, and colleagues are vital members of our extended network. We can lean on them for guidance, in addition to honing our judgment and intuition along the way. And these decisions are deeply personal—they connect to our feelings of worthiness, self-image, and confidence.

Over the long arc of your career, you’re likely to have managers you’d work for again, and managers you’d be delighted never to see or hear from again. I hope you have more of the former than the latter.

During the summer of my sophomore year, I secured an internship at Convergys in Jacksonville, with the goal of receiving a full-time offer upon graduation. I was an IT major and looked forward to putting theory into practice at my first corporate job.

Upon arrival, I learned that my internship project was decidedly non-technical in nature. The people I was working with were lovely, but technologists they were not. To make matters worse, I was earning a full $5/hour less than my intern friends in other departments and companies. Not good.

I’ll spare you the details of my first project—an FMLA data consolidation and documentation project I affectionately called “alphabetizing paperclips”—but I was highly motivated and made the most of my two summers with the company.

To wit, I networked and took on extra work like a madman.

I helped organize the inaugural intern symposium at the company headquarters in Cincinnati, met with executives across the firm, and ultimately secured an extension on my internship that was in line with my professional ambitions.

There was just one problem. I hadn’t told managers what I was doing.

My immature calculus was as follows: I was solely responsible for my success. And I didn’t want to rock the boat. However noble my self-sufficient intentions were, the impact is that I came across as unfocused and secretive.

I still cringe when I met with my managers at the end of the summer to share the news of my internship extension. Awkward doesn’t begin to describe it. They knew, but they were annoyed and confused by how I went about it.

The team at headquarters was excited about this motivated intern down in Jacksonville who had dreams of a thriving career with the company, but the team I worked with every day had to find out about my ambitions through their colleagues.

I didn’t realize that my team could have been a force multiplier for my efforts. They already knew all the people I was meeting. My “win” felt hollow, and I strained relationships I valued.

If I could counsel my young, ambitious self, I’d say something like this:

Listen, Will. I know you feel like you need to hustle and make something happen here, but the real work isn’t the outcome of the internship. It’s how you move through it.

Your manager is here to support you, and if something isn’t working as you had hoped, schedule some time on her calendar and ask for advice. You don’t have to do it alone.

Work with the system—not around it—and watch doors open that you didn’t know were available to you.

Managers have a significant impact on your career and work experience. They can eliminate obstacles in your path, offer timely guidance on things you’re not seeing, and put in a good word for you with the right people.

I did things the hard way that summer. Don’t be like me.

Bring your people along.

I was rounding the final corner on my walk to the gym in downtown Brooklyn when a baseball fell from the sky and thudded onto the sidewalk in front of me.

Across the street was a recreational field where someone had accidentally hit a ball over the twenty-foot fence. I looked over, and a guy with a baseball glove looked on curiously to see if I was going to spare him an inconvenient walk to retrieve the product of his son’s athleticism.

Secretly delighted, I dropped my backpack and wondered if I could at least get the ball over the fence and in the general direction of my new teammate.

Baseball never excited me growing up, I was a basketball guy through and through—blame it on the whole 6’3 thing. I played baseball during PE classes in elementary school, sure, but basketball was my chosen sport.

I sent up a silent prayer to Roberto Clemente and let it fly.

The ball sailed over the road, cleared the fence, went between the trees where the guy was standing, and he caught it—he didn’t even have to move. I played it off as if it wasn’t a big deal, but I felt like Neo in the Matrix when he learned that he could dodge bullets.

It’s been at least a year and a half since my moment of spectacular arm cannon excellence, but I still smile every time I think about it. In my storytelling workshop called My Beautiful Story, I describe everyone as the hero of their own journey, and how this posture is a catalyst for connection and empathy. I definitely felt like a hero that day.

We all have experiences and accomplishments that we fail to or forget to share with others, and it’s a gift to create the space where people have an excuse to share them.

When I was in fifth grade, my friend and I had a problem: we needed cash, probably for video games. As we brainstormed business ideas in John’s backyard, we noticed what appeared to be mistletoe growing on one of his trees. Uh, cha-ching?

An hour later, two budding horticulturists hit the streets with their wares.

Our door-to-door sales experience was a raging success. I don’t remember how much we made, but it was more than we started with. We could have earned more, but we ran out of product, and it was quitting time (my mom picked me up).

The lesson that stuck with me from that experience wasn’t the success, though—it was the dad who wasn’t impressed.

We knocked on his door, fully expecting to blow him away with our entrepreneurial zeal and well-timed offer. It was December, after all, which is objectively mistletoe season.

But I remember him critiquing the bundles and the fact that the remaining ones had berries that were more green than white. A bit less festive, I guess. He prodded a few bundles skeptically and muttered about us not having a higher quality product.

I was shocked. Didn’t the Dubious Dad see how adorable we were? Didn’t he realize that his one job was to enthusiastically toss us a few pesos in support of a local black-owned business? We were kids!

I don’t think he bought anything that day, but the lesson he gave me was far more valuable: our work product has to stand on its own merits.

It’s easy to convince ourselves that people should buy from us because we want them to, but busy strangers are sometimes impervious to our charm and desire to relieve them of their discretionary funds. For many of us, that means we just have to try harder.

In the last 10 minutes of an executive session I was leading, I had to make a decision. I wanted to tie a nice bow around the morning and give the group a preview of what our following conversation would entail. But I couldn’t.

“Is this working for you all? It doesn’t feel like this is worth your time.”

You could hear a pin drop.

We still had several more sessions left in our contract, and few leaders wake up in the morning expecting their trusted advisor to try and fire themselves. I gave them a moment to process, and several of them thanked me for having the courage to speak up and invite some real talk before we dismissed.

In the immediate aftermath, several team members went out of their way to ensure I didn’t feel discouraged about the progress of our work. But the truth is that I had never felt more confident in my work and ability to make change.

I’ve been a consultant for my entire career, and I’ve been facilitating executive sessions for nearly a decade. What comes with that experience is a clear understanding of when and where my work is most effective. A lot of it has to do with personality fit, but other factors are equally important: how the team make decisions, how comfortable they feel speaking up, and how open they are to change.

I went in with high hopes, but sometimes our ambitions don’t survive contact with reality. That’s normal. What we do with this realization is up to us.

It would have been a lot easier not to rock the boat, but I was unwilling to trade short-term comfort for long-term misalignment. The outcome? We decided to repurpose the remaining sessions for work with their people managers—work that everyone is excited for me to deliver.

What’s more: the client sees me embodying my values of authenticity, speaking truth to power, and being open to finding creative solutions.

I went to school for Information Technology, and I was among the first to graduate from FSU’s College of Information with that degree. Previously, it was the School of Information, focusing on Library and Information Science. I had good timing.

My first love was medicine—my mom was a nurse, and I still fantasize about completing a medical anthropology doctorate—but my father wisely nudged me in a more practical direction, aligning with my aptitude for technology. In truth, I had no idea what the pursuit of medicine required at the time, and tech was undoubtedly the right specialization for me.

I’ve always been fascinated by web publishing, and I recall looking up williejackson.com in school to see how much it would cost to register the domain. It was an eye-popping $500 for some reason, but I checked back regularly and managed to snag it for a much more reasonable $50 months later.

I still remember my first website and my obsession with the HTML and CSS that brought it to life. I turned that obsession into a freelance web design business after friends coveted my shiny new web presence. I never made retirement money, but I learned about sales, marketing, pricing, and eventually web hosting, which ultimately led to a Director of Web Optimization role. Invaluable.

Anyway, I recently overhauled my website after putting it off for years, and I’m really happy with how it’s coming together. It’s not “finished”—websites are never finished—but it’s live, and I’m happily neck-deep in details that most people will never notice or care about.

And that’s fine by me, it’s just great to be back at it.

Earlier this year, I was facilitating a session on authenticity—a squishy and nebulous term that I had seen used unhelpfully for years. My workshop was well-researched, and I felt prepared, but I still had more than a few misgivings about the topic going into it.

On a lark, as I was putting the session together, I included quotes on authenticity from three very different people. And for reasons unknown, this really section struck a chord with the audience. You could palpably feel the excitement and engagement growing in the room. The session had come alive. The room had come alive. People had a lot to say.

This isn’t an uncommon experience, but it’s always a turning point when I’m presenting something new. I never know when the moment will come, but it’s always a relief when it does. Yes, it felt validating for my experiment to pay off. But the real magic was learning from the audience what authenticity meant to them.

The not-so-secret secret that teachers know is that what looks like the sharing of knowledge is actually them saying, “Here’s something interesting that I’ve learned, what do you think? Is there something interesting here for you?”

There was. There usually is.

About a decade ago, I was meeting with a new client in Manhattan about a project. We were similar in age, shared hundreds of mutual friends, and the project had all the trappings of an experience that would forge a lasting relationship.

There was a lull in the conversation as our kickoff meeting was winding down, and to my utter bewilderment, he started making a series of racial jokes. Not in an exploratory, test-the-waters kind of way—it was a rapid-fire I’ve-been-waiting-for-this-moment vibe.

The jokes weren’t especially offensive, but they were nonetheless shocking and unwelcome. The client happened to be a white guy, but equally important is the fact that this was our first meeting. We had nothing close to the kind of rapport that would make his comments okay.

I didn’t have the patience or sophistication to address it diplomatically, so I asked him what the hell was going on. His face sank as he turned fire engine red.

He sheepishly explained that his primary exposure to black men was as a high school football player, and their way of relating to each other was to crack predominantly racial jokes. He assured me that no harm was intended and that he only meant to poke a little good-natured fun.

Finally, it made sense. Bless his midwestern heart.

Understanding his point of reference and intent allowed me to soften my reaction and view him with compassion; he was doing the best he could using the tools he had and simply trying to connect with me.

It’s easy to believe that people around us harbor animus and overt bias—we’re all living through a destabilizing period of polycrisis—but this makes the need for connection, courage, and community even more urgent.

This week, I delivered a Global Black History Month session for a client I’ve been working with since 2022. The story goes back to 2020, when many organizations were dealing with the racial reckoning following George Floyd’s murder. Sarah saw my MAKERS keynote about the ally skills framework I helped create and reached out on LinkedIn, thinking she’d never hear back. We had our first call 10 days later and our first project 60 days later.

My work as a speaker, consultant, and facilitator isn’t possible without partners advocating for me in rooms I don’t yet have access to. And it’s not like I’m speaking about standard business topics like sales and marketing—I’m often steadying the hand of leaders looking to navigate the tumultuous terrain of race, gender, and difference more generally.

I could write a manifesto on the role an external speaker like me plays when being brought in to deliver a timely message, but here are three that have served me:

• Know your audience: When working with an array of constituents across an organization, I will show up differently in a meeting with the CEO than in a meet-and-greet with the organization’s Black ERG (Employee Resource Group). I’m not a different person on these calls, but the message I’m bringing has to address a different set of unspoken needs.
• Share the spotlight: in my address this week, I asked for brief, recorded videos of two employees in the NYC and London offices talking about their career highlights and challenges. The audience loved this format from a stagecraft perspective and in providing global visibility for people who had the courage to speak personally about their professional experiences.
• Read the room: the worst thing you can do as a speaker is offend your host, and the second worst thing is being forgettable. Dancing without a net is my specialty; audiences appreciate it when you take risks.

But mostly, my job is to make the people who hired me 1) look good and 2) feel glad that they brought me in.